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Chromene compound

a chrome compound and compound technology, applied in the field of chrome compound, can solve the problems of low durability, low fading speed, and strong color development, and achieve the effects of low initial coloration, high double peak characteristic, and high color development sensitivity

Active Publication Date: 2014-02-06
TOKUYAMA CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The present invention provides a chromene compound that has a neutral tint, high color development sensitivity, and low initial coloration. It has a high fading speed and is excellent in durability of photochromic properties. The compound can dissolve in a high concentration and is useful for optical articles. The invention also discusses the effect of different substituents on the color characteristics of the compound and proposes a structure with high electron donating ability at both the 6-position and 7-position that has a high double peak characteristic with low initial coloration and high color development sensitivity. Introducing an electron suction group in the 11-position can further improve fading speed, while introducing a substituent with high electron donating ability can increase the absorption end of the compound but reduces fading speed.

Problems solved by technology

Although the above compound has high double peak characteristic, it has defects such as low fading speed, strong color development by heat at room temperature under no exposure (this color development will be referred to as “initial coloration by thermochromism” hereinafter) and low durability.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

example 1

[0202]1.20 g (2.0 mmol) of a naphthol compound represented by the following formula (22) and 0.80 g (3.0 mmol) of a propargyl alcohol compound represented by the following formula (23) were dissolved in 70 ml of toluene, 0.022 g of p-toluenesulfonic acid was further added to the resulting solution, and the obtained mixture was stirred under reflux by heating for 1 hour.

After a reaction, the solvent was removed, and the obtained product was purified on silica gel by chromatography to obtain 1.35 g of a white powder product. The yield was 80%.

[0203]The elemental analysis values of this product were 78.22% of C, 6.72% of H, 1.55% of N and 3.75% of S which were almost equal to the calculated values of C52H52O6 (C, 78.26%, H, 6.81%, N, 1.66%, O, 9.48%, S: 3.80%)

[0204]When the proton nuclear magnetic resonance spectrum of the product was measured, it showed 18H peaks based on the methyl proton and methylene proton of a tetramethylcyclohexane ring at δ of around 1.0 to 3.0 ppm, 20H peaks b...

examples 2 to 16

[0206]Chromene compounds shown in Tables 1 to 5 were synthesized in the same manner as in Example 1. When the structures of the obtained products were analyzed by using the same structure confirming means as in Example 1, it was confirmed that they were compounds represented by structural formulas shown in Tables 1 to 5. Table 6 shows the elemental analysis values, calculated values obtained from the structural formulas and characteristic 1H-NMR spectra of these compounds.

TABLE 1Raw materialsEx-PropargylampleNaphtholalcoholYieldNo.compoundcompoundProduct(%)277375470

TABLE 2Raw materialsEx-PropargylampleNaphtholalcoholYieldNo.compoundcompoundProduct(%)573674768

TABLE 3Raw materialsEx-PropargylampleNaphtholalcoholYieldNo.compoundcompoundProduct(%)8719681066

TABLE 4Raw materialsEx-PropargylampleNaphtholalcoholYieldNo.compoundcompoundProduct(%)116112721366

TABLE 5Raw materialsEx-PropargylampleNaphtholalcoholYieldNo.compoundcompoundProduct(%)146815601664

TABLE 6Elemental analysis valuesExampl...

example 17

[0207]1.0 g (2.1 mmol) of the following naphthol compound (25) and 0.80 g (3.0 mmol) of the above propargyl alcohol compound (23) were dissolved in 70 ml of toluene, 0.022 g of p-toluenesulfonic acid was further added to the resulting solution, and the obtained mixture was stirred under reflux by heating for 1 hour.

After a reaction, the solvent was removed, and the obtained product was purified on silica gel by chromatography to obtain 1.1 g of a white powder product. The yield was 72%.

[0208]The elemental analysis values of this product were 75.68% of C, 6.70% of H and 8.93% of S which were almost equal to the calculated values of C45H46O4S (C, 75.79%, H, 6.64%, S: 8.80%)

[0209]When the proton nuclear magnetic resonance spectrum of the product was measured, it showed 18H peaks based on the methyl proton and methylene proton of a tetramethylcyclohexane ring at δ of around 1.0 to 3.0 ppm, 15H peaks based on the methyl proton of a methylthio group and the methyl proton of a methoxy grou...

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Abstract

A chromene compound which develops a color of a neutral tint and has little initial coloration, high double peak characteristic and high color development sensitivity, rarely experiences the reduction of color optical density though it has high fading speed, is excellent in the durability of photochromic properties and can dissolve in a monomer composition which will become a substrate for optical articles in a high concentration, and a photochromic curable composition comprising the chromene compound and polymerizable monomers.The chromene compound is represented by the following formula (1).(wherein R3 at the 11-position is a second sulfur-containing substituent selected from the group consisting of thiol group, alkylthio group, alkoxyalkylthio group, haloalkylthio group, cycloalkylthio group, arylthio group, heteroarylthio group, sulfonyl group and sulfinyl group, R1 and R2 at the 6-position and the 7-position are a combination of an aryl group or a heteroaryl group and an electron donating group having a Hammett constant σp of −0.1 or less, or R1 and / or R2 is a first sulfur-containing substituent selected from thiol group, alkylthio group, alkoxyalkylthio group, haloalkylthio group, cycloalkylthio group, arylthio group and heteroarylthio group.).

Description

TECHNICAL FIELD[0001]The present invention relates to a photochromic chromene compound, and use and an intermediate thereof. More specifically, it relates to a chromene compound which is useful as a photochromic compound for photochromic spectacle lenses, and use and an intermediate thereof.BACKGROUND ART[0002]Photochromism is the reversible function of a certain compound that it changes its color swiftly upon exposure to light including ultraviolet light such as sunlight or light from a mercury lamp and returns to its original color when it is put in the dark by stepping its exposure to light. A compound having this property is called “photochromic compound” and used as a material for photochromic plastic lenses.[0003]For the photochromic compound used for this purpose, the following properties are required: (I) the degree of coloration at a visible light range before ultraviolet light is applied (to be referred to as “initial coloration” hereinafter) should be low, (II) the degree...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): G02B1/04
CPCG02B1/041C07D311/78C09K9/02C09K2211/1007C09K2211/1011C09K2211/1088C09K2211/1092C07C323/21G02C7/102G02B5/23C07C2603/94
Inventor TAKAHASHI, TOSHIAKITAKENAKA, JUNJIMOMODA, JUNJITERANISHI, KAZUHIROSANDO, MITSUYOSHIIZUMI, SHINOBU
Owner TOKUYAMA CORP
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